The name Machiavelli is so instinctively associated with the dark arts of political expediency that it is hard to conceive of the eponymous writer as a poet, playwright, carnival songster and humanist. But if he has suffered from the fame of his most lasting work, it is equally possible that this work has itself been misunderstood for the best part of 500 years, a process that began almost as soon as he died.

Machiavelli came from a largely powerless but formerly influential family in Florence, at the time one of several significant and independent city-states within the country now known as Italy. These cities were either at each others’ throats, or had another power at their own. The Vatican, the French, the Spanish and the Holy Roman Empire were all hunting for power, influence and control. Rulers and republics (of a sort) came and went with alarming frequency, allegiances and alliances were dissolved as soon as they were formed, and militias and mercenaries added to the factional confusion. Machiavelli, however, both rose to prominence and fell from grace because of a loyalty to his home city, which suffered precisely the complex shifts in fortune of the rest of the country.

The Medici family had governed in Florence for 60 years, but the French invasion of 1493 saw it ousted, and a strange combination of a theocracy and democracy established under the zealous reformer Savonarola. Machiavelli had been living in the city and possibly working as a banker, but seems to have been known as a thinker and humanist. When the Florentines decided to revolt against Savonarola in 1498, they executed him (outside Machiavelli’s office) and proclaimed a republic. Machiavelli was given a senior administrative post and a significant role in the matter of negotiation and diplomacy, rising to second chancellor and secretary to the ten, who were essentially the second tier of the city’s government. Machiavelli had no former experience of such responsibilities, and his elevation may have been because of an involvement with the overthrow of Savonarola, or the fact that one of his former teachers was a senior member of the new governing body. But once in place, he continued to serve his republican city for the next 14 years, travelling on more than 20 missions to Rome, Germany and France. As a result, he became not only intimately acquainted with the niceties and nuances of diplomacy, he also saw first hand the way that other principalities and kingdoms functioned, how they achieved power and held on to it, and how the people regarded their rulers. In 1502 he married Marietta Corsini. They had six children, and remained close (despite his mistresses) until his death. But 1502 was significant for other reasons, too. It was the year Piero Soderini (a man to whom Machiavelli was to become close over the next decade) effectively became head of state; and it was also the year in which Machiavelli was sent to observe—in an official capacity—the great and powerful duke Cesare Borgia, son of Pope Alexander VI.

Borgia was in the process of creating a new state by taking over several smaller ones, with the considerable help of the Vatican. He was cruel, brave, brilliantly statesmanlike and viciously duplicitous. He managed to keep newly conquered states under his control and was often seen as an improvement on the rulers who had been there before. This duke was the epitome of political realism, and one whose example might profitably be copied. But Machiavelli was also reminded that political life is transient: when the pope died suddenly, the Borgias’ influence and power dissolved.

Despite the pressing nature of much of his work, including the development of a Florentine militia, Machiavelli had started to write in the early 1500s, his work including verses, histories and comic dramas. Throughout his professional career he had been compiling reports, writing letters, notes, memorandums and articles of policy, in all of which his political understanding was becoming surer and more complete. He had always had a love of history and drama as well, with a deep reverence for the classical authors, and it was not long before he would need whatever consolations philosophy could provide.

The Florentine government was weakening and European events were conspiring to make the city vulnerable. With the usual suddenness of such matters, the Spanish defeated the Florentine army at Prato, Soderini’s party fell, and the Medicis came back to rule the city in 1512. Machiavelli, as a senior man at the side of Soderini, was sacked, falsely accused of involvement in a conspiracy, imprisoned, tortured and finally exiled. Needless to say, the violence and shifts in power didn’t stop there. The Florentines again ousted the Medicis in 1527 but Machiavelli, by then to some extent back in favour, was too ill to be part of the movement; he died just a month after the republic was proclaimed.

He had seen governments change hands dramatically, had watched princes and rulers gain and lose power, had served a republic and watched the influence of kings and popes. In his exile, he had time to think and write. But this suggests a man of instinctively studious and sedentary habits, retiring to compose his memoirs. Machiavelli was more imaginative, active, vigorous, even earthy in his complex humours, than that. There is a sense of questing for a more stable future for northern Italy in his political writings (The Art of War, his Discourses), quite apart from the frankly indecent aspects of some of his other works (although Mandragola was considered one of the best plays of the century). The Prince was available as early as 1513, although it was not formally published until 1532, but its nature and intent remain ambiguous. Almost as soon as it was published, it was either banned or demonised because of its suggestion that any means are legitimate, even honourable, in creating a stable government; and also that the governed deserve no better than such treachery as might be exercised by the ruler. It was not translated into English until 1640, but its reputation preceded it to such an extent that its author became associated with diabolical intentions and amorality, and probably gave his name to the expression ‘Old Nick’.

This Mephistophelean simplification is unjust. Machiavelli spent his life in the service of a republic and was a broad-minded intellectual. On the other hand, he did want to get back in favour with the Medicis; so was this his way of attempting it? If so, it is a curious method: it is hardly a work designed to unqualifiedly flatter, and it remained unpublished until after his death and the removal of the Medicis. He wrote other satires... could it be ironic? Or could it have been intended to tell the populace what really motivated their rulers? ThePrince is complex, intriguing, ambiguous and a priceless insight into 16th century politics; but those who read it merely as a guide to successful governing are saying more of their own immorality than Machiavelli’s.